Two-Week Italy Self-Drive Road Trip With Itinerary from Milan to Como, Verona, Venice, Florence, Siena, and Rome

Day 2 of your road trip across Italy promises a magnificent time exploring what to see in Milan. You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

One of the most iconic spots you can visit today is Navigli. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Duomo Di Milano Museum brings Milan's character to life. This history-steeped church is a highlight of any visit in the city. Then, enjoy Galleria Vittorio Emanuele Ii, another romantic attraction that never fails to captivate visitors. Next, head over to Sforzesco Castle Art Library, one of the city’s most impressive attractions, known for its picture-perfect features.

If you’re looking for more, spend time soaking in the atmosphere of Parco Sempione. This eye-catching park is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Gae Aulenti, a captivating public square, and take a stroll around the area.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

Bring home unique finds from Milan's bustling shopping hub, Via della Moscova. Enjoy a leisurely exploration of unique boutiques and stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Via della Moscova offers plenty of options, including cafes, primary services, unique landmarks, and community events.

Milan is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Milan.

Don’t miss out on dining at Dessert Bar Milano, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Radisson Blu Hotel Milan, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Qui Si Mangia. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

Continue the enjoyment post-dinner at Kilburn Cocktail Bar Milano, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Frida offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out The Friends Pub Milano. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Head back to your accommodation in Milan and get some rest to prepare for another magical day of your road trip in Italy.

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 4 destinations, including Como, Rogaro, Lenno, and Colonno. At the end of the day, you’ll unwind at one of the finest accommodations in Como, where you'll spend 1 night.

Let Basilica Di San Fedele set the tone for the day. Spend some time admiring this culturally significant church before continuing your journey. Saint Mary Assunta Cathedral is your next stop. This captivating church is one of the best-rated sights in Milan.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Villa Carlotta (lake Como). This visually striking museum is a sight to behold. To round off your sightseeing experience, visit Villa Del Balbianello and Greenway Del Lago Di Como.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Como. Como offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

After a day of adventure, treat yourself to an exquisite dinner at one of Como's best restaurants.

Enjoy a delicious meal at L’Antica Trattoria, a highly-rated dining destination in Como. If you're eager to try something different, consider Gesumin Restaurant, another top spot with a tantalizing menu. You might also want to secure a reservation at Pronobis. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Como this evening.

Continue your lively evening at Fresco Cocktail Shop, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Il Cortiletto is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Pinocchio ensures a night out tailored to your taste.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Your itinerary for day 4 of your road trip in Italy includes 1 stop and features some of the highlights of Verona. At the end of the day, enjoy the comforts of a top-rated hotel in Verona, where you'll spend 1 night.

Make a stop at Giusti Garden. This often recommended botanical garden is a must-visit for travelers looking for a unique holiday experience. Make your way to Ponte Pietra located in Como for another exciting encounter.

Next, immerse yourself in the setting of Piazza Dei Signori. Its enchanting features will captivate you. After the public square, continue your tour of the city with a visit to Piazza Delle Erbe. Visitors usually appreciate the enchanting features of this public square. Next up is Castelvecchio Museum, a highly recommended museum. For a change of pace, head to Verona Arena. As one of the most globally renowned attractions in Como, this stadium is the perfect place to end your self-guided sightseeing tour.

When you’re done exploring for the day, you’ll drive to your hotel in Verona. Check in and relax before you head out to tour the city.

Verona is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Verona.

Have a fantastic dining experience at La Griglia, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Vecio Macello offers an enticing alternative with its varied menu. Additionally, Via Fama Cafè | Verona is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Verona.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Archivio stands out as an excellent choice for a post-dinner cocktail. Alternatively, La Segreteria Café offers an ideal atmosphere to enjoy the pleasures of the night. Grande Giove Cocktail Bar is also a great option that provides a perfect setting for a relaxing evening.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Venice. At the end of the day, you will retreat to the hotel of your choice in Venice, where will spend 2 nights.

One of the most beloved attractions included on the itinerary is Santa Maria Della Salute. This visually striking church will help you start your sightseeing on top. Then, take a leisurely stroll to Peggy Guggenheim Collection and learn what makes this history-steeped art gallery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the beloved Santa Maria Gloriosa Dei Frari. After exploring the church, head to Grand Canal. This increasingly popular street is a highlight in Verona.

At the end of the day, you will drive to Venice, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Venice, it's often a good idea to reserve a table in advance.

Don’t miss out on dining at Bauer Hotel, a top-rated dining destination in Venice. If you're in the mood to try something new, consider L'Osteria Le Guglie, another top spot with a mouthwatering menu. You might also want to secure a reservation at Corner Pub. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Venice this evening.

Keep the excitement of the evening going by visiting a bar or two. Al Parlamento is an excellent place to start. You could also check out The Caffe Rosso, offering a different kind of charm. A last recommendation for the day is Adagio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Relax and look forward to more memorable moments to come!

Day 6 of your road trip will take you to the best attractions Venice has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Venice.

Whether you decide to explore Venice on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Let Rialto Bridge set the tone for the day. Spend some time admiring this visually striking historical landmark before continuing your journey. Teatro La Fenice is your next stop. This interesting opera house is one of the best-rated sights in Venice.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Piazza San Marco. This romantic public square is a sight to behold. To round off your sightseeing experience, visit St Mark's Basilica and Doge's Palace. If time allows, end your day with Bridge Of Sighs, a visually striking monument that offers a memorable conclusion to your exploration.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Venice. Enjoy a relaxing evening as you savor delicious local cuisine.

Enjoy a delicious meal at Generator Venice, a highly-rated dining destination in Venice. If you're eager to try something different, consider Nevodi, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante La Piazza. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Venice this evening.

Explore the vibrant nightlife at Il Mercante after your meal, a hub for lively evenings and memorable moments. Or, head to The Irish Pub Venezia for a great selection of flavorful drinks and a charming setting. Furthermore, Ai Stagneri is perfect for those looking to extend their night with a touch of local flavor.

Take some time to reflect on your day and savor another beautiful night in Italy.

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Florence. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 3 nights.

Piazzale Michelangelo leaves a lasting impression. This observation deck is one of the most spectacular places to visit in Venice. Next, head to Basilica Of Santa Croce In Florence, a captivating church, known for its standout features.

Nearby, you'll also find Central Market and Cathedral Of Santa Maria Del Fiore. Visit these for an interesting touch to your journey.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Florence. Florence offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Make sure to reserve a table at Ristorante Oliviero 1962, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Di Poneta Novoli, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your evening by exploring the vibrant nightlife scene at Manifattura, a prime destination for a thrilling night out. Also, don’t forget to check out Se·sto On Arno Rooftop Bar, a bar that offers unique local touches. Likewise, Il Vinile provides an excellent alternative for a fun evening.

Take some time to reflect on your day and savor another beautiful night in Italy.

Day 8 offers an itinerary packed with the best things to see in Florence. You’ll stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Set aside time today to explore Oltrarno, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Enjoy all that Ponte Vecchio has to offer. This is an iconic historical landmark you should not miss. Another must-see is Piazza Della Signoria, a top-rated public square in Florence.

When you’re ready for the next sight, head to Bargello National Museum. From there, take a leisurely stroll to Palazzo Vecchio, another of the city’s captivating attractions. We recommend continuing your self-guided tour at Uffizi Gallery, a picture-perfect place of interest in the city.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Continue your evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.

Savor another day of unforgettable experiences in Italy!

Wake up to day 9 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Pisa. With 1 night to stay in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Check out the increasingly popular church, Santa Maria Della Spina. Afterward, continue to Knights' Square, a public square every traveler should visit. As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Leaning Tower Of Pisa. This world-famous monument is an essential stop. Following that, head to Pisa Cathedral, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Del Duomo, Pisa, a globally renowned public square in the city. Finally, end your day with a visit to Campo Santo, a historic cemetery that offers the perfect conclusion to your sightseeing of the day.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Don’t miss out on dining at Ristorante Buca Mario, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Agricola Toscana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

If you’re not ready to end the night just yet, Gosh* offers a perfect venue to relax and savor a drink. Similarly, Antico Caffè Del Moro - Art Bar Firenze is well-suited for those looking to unwind in a social setting. Quelo Bar is another excellent spot to enjoy a nightcap after a delightful meal.

Celebrate another amazing day of your road trip adventure in Italy!

On day 10 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Siena are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Porta Romana brings Florence's character to life. This breathtaking monument is a highlight of any visit in the city. Then, enjoy Palazzo Salimbeni, another eye-catching attraction that never fails to captivate visitors. Next, head over to Basilica Of San Domenico, one of the city’s most worthwhile attractions, known for its grand features.

If you’re looking for more, spend time soaking in the atmosphere of Siena Cathedral. This history-steeped church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Pubblico Palace, a frequently visited palace, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Del Campo before you head back to your hotel.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and relax before you head out to tour the city.

Indulge in a memorable dining experience at one of Siena's most popular restaurants, and connect with friendly locals for a true cultural experience.

Enjoy a delicious meal at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass to another unforgettable day in Italy!

Dive into day 11 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Rome. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 3 nights.

Whatever your travel style is, Colosseum is an essential stop in Siena. This iconic archeological site provides an insightful glimpse into the city's identity. Next, discover Roman Forum, an UNESCO world heritage-designated archeological site, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Del Popolo, an astonishing public square. When you’re done, don’t forget to make a stop at the interesting Capitoline Museums.

At the end of the day, you will drive to Rome, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Dine in style at La Bottega Roma, a top recommendation for dinner tonight. Or, for a change of pace, Pasta In Corso boasts a menu that's sure to impress. Also, be sure to check out Trattoria Vecchia Roma. Known as a local hotspot, it’s a great choice for tonight in Rome.

Unwind after your meal by stepping into La Botticella Of Poggi Giovanni. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Almalu Trastevere offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Viminale Di Pepi Maurilio, another top-rated bar in the area.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

Greet day 12 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 2 nights to stay in Rome, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Vatican City and Rome.

Whether you decide to explore Vatican City on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Make sure to visit Trastevere, a popular neighborhood in Vatican City. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

Vatican Museums leaves a lasting impression. This art museum is one of the most timeless places to visit in Rome.

Nearby, you'll also find Campo De' Fiori and Piazza Navona. Visit these for an interesting touch to your journey.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Rome.

After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

Treat yourself to a wonderful meal at RomAntica, a top-rated dining spot in Rome. If you're in the mood for something new, try Coso Ristorante, another premier location with a delectable menu. You might also want to book a table at DEROMA - Farine Romane. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Say good night to Rome and look forward to another great day of your road trip in Italy!

On day 13 of your road trip, you will have an entire day to discover what to see in Rome. You’ll stay in Rome for 1 night.

Whatever your travel style is, Basilica Of San Clemente is an essential stop in Rome. This locally appreciated church provides an insightful glimpse into the city's identity. Next, discover Spanish Steps, a majestic public square, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Di Spagna, a wondrous public square. When you’re done, don’t forget to make a stop at the world-famous Trevi Fountain. Not far away from the monument, you will find the enchanting Castel Sant'angelo, perfect for a quick visit. Round off your day at Pantheon, another gem in Rome with culturally significant features to discover.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Rome, it's often a good idea to reserve a table in advance.

Treat yourself to a delicious dinner at Hotel de Russie, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss The Parrot Bar. Known for great service, it’s a fantastic choice for tonight in Rome.

If you’re not ready to end the night just yet, The Apartment Bar Roma offers a perfect venue to relax and savor a drink. Similarly, Hotel Hassler Roma is well-suited for those looking to unwind in a social setting.

Relax and look forward to more memorable moments to come!

Your itinerary for day 14 of your road trip in Italy includes 1 stop and features some of the highlights of Bologna. At the end of the day, enjoy the comforts of a top-rated hotel in Milan, where you'll spend 1 night.

Bologna Cathedral makes a great addition to your morning plans. This up-and-coming church is a monumental place to see in Rome. Continue your discovery at Piazza Maggiore, an enchanting public square with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Two Towers. This notable monument offers a culturally significant encounter with Rome. Next, make your way to Porta Maggiore to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Milan. Milan offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

After a day of adventure, treat yourself to an exquisite dinner at one of Milan's best restaurants.

Enjoy a lovely meal at Bice Restaurant, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Alto Ristorante is another top choice with a popular menu. You could also check for a table at Nero 9. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Milan tonight.

Continue the enjoyment post-dinner at Bhangrabar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Rufus Cocktail Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Ostello Bello Grande. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Say good night to Milan and look forward to another great day of your road trip in Italy!